Providing accessibility information about sidewalks for people with difficulties with moving is an important social issue. We previously proposed a fully supervised machine learning approach for providing accessibility information by estimating road surface conditions using wheelchair accelerometer data with manually annotated road surface condition labels. However, manually annotating road surface condition labels is expensive and impractical for extensive data. This paper proposes and evaluates a novel method for estimating road surface conditions without human annotation by applying weakly supervised learning. The proposed method only relies on positional information while driving for weak supervision to learn road surface conditions. Our results demonstrate that the proposed method learns detailed and subtle features of road surface conditions, such as the difference in ascending and descending of a slope, the angle of slopes, the exact locations of curbs, and the slight differences of similar pavements. The results demonstrate that the proposed method learns feature representations that are discriminative for a road surface classification task. When the amount of labeled data is 10% or less in a semi-supervised setting, the proposed method outperforms a fully supervised method that uses manually annotated labels to learn feature representations of road surface conditions.